ABOUT US 2018-01-18T09:35:32+00:00

Windy City Sailing Inc. was established in 2004 and since then has been offering world class private charters on Lake Michigan. Our motto is to offer an immaculate yacht, first class customer service and great value for your money!

Our Captains: all are licensed by the United States Coast Guard

Captain Josef: Fell in love with sailing while living in San Francisco and now spends his summers on the water either sailing with clients or racing. His thoughts on sailing………

I have always been drawn to the water for as long as I can remember.  I was living in San Francisco in the late nineties and it was there that I was introduced to sailing.  Learning how to sail in the bay, with the Golden Gate Bridge in the backdrop kindled my love for sailing.  I have been an avid sailor ever since. I moved back to Chicago a couple years later and wanting to stay as active as possible got my captains license in 2002 so I could captain bareboat charters for various programs that sailed on Lake Michigan and Caribbean. 
Windy City Sailing was started in 2004, when I partnered into a sailboat with a friend who was also an avid sailor. While difficult to put into words, the feeling on being on a sailboat brings a sense of freedom and simplicity like no other.  It can be anything from a peaceful break from the daily grind, or the most enjoyable way to spend an afternoon or evening with family and friends.  It brings me genuine happiness to share the beauty of sailing with people.  The next year, I purchased our flagship yacht, Nebula, a Beneteau 393. 
Aside from sailing recreationally and captaining charters, I race with a crew on a J111 and have done 8 races from Chicago to Mackinac Island.  At 330 miles, the Mac Race is the longest freshwater race in the world.  In 2010, we took 1st place.  We also participate in the NOOD and Verve Cup every summer.  I find that while racing has honed my technical skills it’s been the camaraderie of the crew that has been the most fun.
I live in Hawaii now with my family and we spend the summer months in Chicago.  The first time I had ever been to the Hawaiian Islands was in 2004 after sailing from San Diego to Oahu to deliver a sailboat for a friend.  It took 17 days to cross 2400 miles, and what an incredible experience it was.   I have had the privilege of sailing in a few pretty amazing places in the world – the British Virgin Islands, Tahiti.  But I have to say that Lake Michigan holds a special place in my heart.  There is nothing quite like a warm summer night, the beautiful skyline in the background and the wind in your sails.

Captain Gentre: With more than 30 years sailing experience, Gentre is very well versed in all things sailing and has some thoughts on the pleasure of sailing…….

Sailing allows us to leave the City and be in a new environment shortly after leaving the dock.  When we get the sails up an turn off the engine, a rush of relaxation waves over the cockpit.
One of the joys of being a Certified Captain is safely bringing that joy to others.   Each group is different.   Some like the spectacular views of the City Skyline and others the Fireworks on Wednesday and Saturday nights,  Some want to learn to sail and others just want to relax with a refreshing beverage.
Having sailed the Great Lakes for over 30 years and a 50 Ton Master Captain for the last three years, it is pleasure to provide the type of experience our guests desire.   Knowing the best places to watch the Fireworks and the various landmarks such as Buckingham Fountain and Navy Pier are greatly appreciated.
Of course wedding proposals, often in conjunction with a B & B overnight are the most fun.  It is amazing to see how thoughtful the guys are that have elected to propose on a private cruise.    Often they will provide a catered dinner with chef and flowers prior to proposing on the bow of the boat— sometimes during the Fireworks.    Being able to witness the event from a discreet distance back at the wheel is a true pleasure!

Captain Mike: Sailing the waters of Lake Michigan for more than 20 years, he is a Chicago Fireman with a passion for bringing the joy of sailing to Windy City Sailing clients.